This is the weekend the Hamptons turns on. Memorial Day is the unofficial start of summer on Long Island, and every signal of the season comes on at once. Gurney's and the Montauk Yacht Club open their summer programming Friday. Westhampton Beach hosts its Festival of the Arts both days. Jones Beach goes big with reenactors, live music, and a patriotic drone show over the Atlantic. Old Bethpage Restoration Village runs a full living-history weekend with a Memorial Day parade Sunday. Splish Splash opens for the season. And the LIE and Sunrise Highway eastbound on Friday afternoon are about to teach a lot of new drivers what Hamptons traffic actually feels like.

Here's what's worth planning around — with the parking and traffic reality for each.

Hamptons Memorial Day Opening Weekend

Friday, May 22 – Monday, May 25 | Southampton, East Hampton, Montauk, Sag Harbor

Memorial Day weekend is the Hamptons season opener and the calendar is packed. Marina St Barth celebrates its 20th anniversary at its new Southampton location Saturday afternoon from 3pm to 6pm. The Baker House 1650 in East Hampton runs its Sunset Aperitivo in the gardens Sunday from 3 to 6pm. Dan's Rosé Soirée lands Sunday evening at 6:30 at the Southampton Arts Center — local rosé from regional wineries, restaurants, and DJs. Gurney's in Montauk and the Montauk Yacht Club both open their full summer programming Friday through Monday: live music, firepits, dive-in movies, surf lessons, the whole rollout. Sag Harbor Cinema kicks off its "Summer Noir" festival.

The traffic on this is the single most predictable thing on Long Island all year. Eastbound Sunrise Highway on Friday afternoon is gridlocked from exit 50 through Hampton Bays. Saturday morning eastbound between Manorville and Southampton is the slow stretch as the weekenders who didn't beat the Friday surge try to make up for it. Sunday evening westbound is the same picture in reverse — anyone leaving the Hamptons between 4pm and 8pm on Sunday is sitting in it.

We run this weekend constantly. A couple booking a Sag Harbor hotel Friday night through Monday morning gets the round trip handled — drop on Friday, pickup Sunday or Monday, no driving home tired through a Hamptons traffic jam at 9pm. Corporate groups renting a Southampton or Montauk house for the holiday weekend book the same setup for the whole group — single drop, single pickup, and the JFK or LGA airport runs out from the house Monday or Tuesday. Our Sprinter van service is the right answer for groups of six to fourteen heading out together.

Jones Beach Memorial Day Celebration — Patriotic Drone Show

Saturday, May 23 – Monday, May 25 | Jones Beach State Park, Wantagh

Jones Beach goes big for Memorial Day. The state park runs a multi-day celebration with a historical reenactor village, colonial trade demonstrations, live music, lawn games, inflatable bouncers for kids, and a patriotic drone show over the Atlantic as the grand finale. It's free with park admission. This is one of the biggest family events on the South Shore all year and the weekend Jones Beach starts to feel like summer.

The parking situation at Jones Beach on a sunny Memorial Day weekend is the predictable problem. The Field 4 and Field 6 lots are the closest to the boardwalk where the celebration sets up, and they fill by mid-morning. The Wantagh Parkway south through the toll plaza backs up Saturday and Sunday from 10am onward. If you're hitting the drone show specifically — typically scheduled for sunset — you're parking on the far end of the lot and walking 15 minutes back.

For a family from Garden City, Hicksville, or Massapequa, this is a 20 to 30-minute drive most days. On Memorial Day weekend that doubles, and on the return trip after the drone show, the Wantagh Parkway northbound at 9:30pm is its own kind of jam. A car service handles the drop right at the entrance and the pickup at the same spot when the show wraps, no driving home in the dark on a Parkway full of beach traffic.

Old Bethpage Restoration Village — Memorial Day Living History Weekend

Saturday, May 23 + Sunday, May 24 | 10:00 AM – 4:00 PM | 1303 Round Swamp Road, Old Bethpage

Old Bethpage Village Restoration runs a full Memorial Day weekend of living history. Period trade demonstrations, fiddle and dulcimer and banjo music throughout the day, a Memorial Day ceremony with a parade through the village at 2:15pm Sunday, and the full 19th-century working village open for the weekend. This is the local family go-to for the holiday weekend on the Nassau side — easy, walkable, and unlike most Memorial Day events, it actually commemorates the holiday rather than just selling beach towels.

Parking is on-site at the village and the lot is large enough for normal museum days, but the Memorial Day weekend draws a real crowd. The lot fills by 11:30 Saturday and 10:30 Sunday with the parade audience. The site itself is set up for walking — wear shoes that can handle uneven ground and grass.

For Nassau County families this is a 15 to 25-minute drive most of the time, and the drive itself isn't the problem. The transportation question only matters if you're combining Old Bethpage with another stop — a Long Island Children's Museum trip, dinner in Massapequa, or a connection to a Jones Beach evening drone show. Otherwise, it's an easy local day.

Westhampton Beach Festival of the Arts

Saturday, May 23 + Sunday, May 24 | Main Street, Westhampton Beach

Westhampton Beach kicks off its summer with the Festival of the Arts, a two-day outdoor gallery that takes over Main Street. Painters, photographers, glass artists, and jewelers from across the country set up booths along the village. Free to walk in. It runs both days from late morning into the afternoon, and the downtown Westhampton Beach village is at its best with the restaurants and shops open and the weekenders just starting to arrive.

The parking situation in Westhampton on Memorial Day weekend is exactly what you'd expect. The village lot fills early both days, and street parking on Main Street and Mill Road becomes a hunt by noon. The smart move is parking a few blocks out at the public lots near the Performing Arts Center and walking in. If you're combining the festival with lunch at Annona or Westhampton Steakhouse, plan the parking before the meal, not after.

For a Suffolk County family from Patchogue or Bayport, Westhampton is 30 minutes on the Sunrise. From central Nassau it's 50 to 60. The return westbound Sunday afternoon is the slow part — Hamptons traffic doesn't differentiate between someone heading home from Montauk and someone heading home from a Westhampton art festival.

Smithtown Spring Craft Fair

Saturday, May 23 + Sunday, May 24 | Smithtown Historical Society Grounds, Smithtown

The Smithtown Historical Society runs its Spring Craft Fair both days of Memorial Day weekend on the grounds. About 100 local craft and gift vendors, food trucks set up across the property, and the historical buildings open for browsing. This is the kind of low-key Memorial Day weekend event central Suffolk County families default to when they're not driving east — easy, free admission, walkable, and the weather is finally cooperating.

Parking is on the grounds and at the Smithtown Library lot across the street. It fills slowly through the morning and you'll get a spot most of the day. The drive from Stony Brook, St. James, or Nesconset is 10 to 15 minutes. From Hauppauge or Commack it's the same. This one is local, easy, and doesn't need a car service for most people. Worth mentioning only because it's the right Saturday plan if you're staying on the central Suffolk side of the island while the rest of the world heads east.

American Airpower Museum — Legends of Airpower WWII Warbirds

Saturday, May 23 + Sunday, May 24 + Monday, May 25 | American Airpower Museum, Republic Airport, Farmingdale

The American Airpower Museum kicks off its summer flying season with the Legends of Airpower WWII Warbirds weekend. Restored WWII fighting aircraft take to the skies over Republic Airport across the three-day weekend — the museum's P-47 Thunderbolt, the C-47, the Trojan, plus visiting aircraft and ground demonstrations. For aviation families, this is the best three-day weekend the museum runs all year.

Parking is at the museum lot and in overflow at the Republic Airport public lots. It fills mid-morning both Saturday and Sunday. The Republic Airport area has a couple of useful adjacent stops — Adventureland is a five-minute drive south, Tanger Outlets Deer Park is ten minutes east — that turn this into a full day.

For Nassau or western Suffolk families this is a 15 to 25-minute drive. The transportation question really only kicks in if you're combining the Warbirds weekend with a Hamptons trip or an airport ride later. Otherwise, drive yourself.

Getting Around Long Island This Memorial Day Weekend

The Sunrise Highway eastbound Friday afternoon through Saturday morning, and the same road westbound Sunday afternoon through Monday evening, are the predictable bottlenecks. If you're heading to the Hamptons, leave Long Island before 11am Friday or after 9pm. If you're coming back, leave the Hamptons before 11am Sunday or after 9pm Sunday.

For Jones Beach, the Wantagh Parkway south backs up by 10am Saturday and Sunday. Coming back after the drone show is its own jam — plan on 45 minutes from the lot to the Southern State.

For Old Bethpage and Smithtown, the parkways stay clean all weekend. These are easy local drives.

For Westhampton Beach and the American Airpower Museum, the LIE moves fine Saturday morning eastbound. The slowdown is the Sunday return.

We cover all of it — airport transfers, corporate travel, and weekend trips out on Long Island. Whether it's a Hamptons opening weekend run, a Jones Beach evening drop with pickup after the drone show, or a Monday morning JFK ride after the holiday weekend wraps, the process is the same. Request a quote here and we'll handle the rest.

Best Things To Do on Long Island This Weekend — May 23–24, 2026